Towards Redox-Driven Unidirectional Molecular Motion

Hella Logtenberg, Jetsuda Areephong, Jurica Bauer, Auke Meetsma, Ben L. Feringa, Wesley R. Browne*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

15 Citations (Scopus)
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Abstract

Redox-driven molecular motion is an attractive alternative to light-driven processes. Here, the ability of an overcrowded alkene-based unimolecular light-driven rotary motor (A) to be driven by oxidation/reduction cycles is explored. We show that two-electron oxidation of A is followed by irreversible deprotonation and reduction to form a monocationic species D+, in which the stereogenic center is lost. This latter species was isolated through preparative electrolysis and its structure was confirmed by using single-crystal X-ray analysis. However, at short timescales and in the absence of Bronsted acids, these processes can be outrun and the oxidation of A to a dicationic species B2+ occurs, in which the central double bond (the axle of the molecular motor) becomes a single bond; when followed by rapid reduction, it results in the reformation of A, potentially in both its stable and unstable conformations. The latter conformation, if formed, undergoes thermal helix inversion, completing a rotary cycle. The data obtained regarding these reactions provide a window of opportunity for the motor to be driven electrochemically, without degradation from chemical reactions of the oxidized motor.

Original languageEnglish
Pages (from-to)1895-1901
Number of pages7
JournalChemphyschem
Volume17
Issue number12
DOIs
Publication statusPublished - 17-Jun-2016

Keywords

  • cyclic voltammetry
  • electrochemistry
  • electrochromism
  • molecular switching
  • photochromism
  • SINGLE STEREOGENIC CENTER
  • MOTORS
  • SWITCHES
  • DITHIENYLCYCLOPENTENES
  • EFFICIENCY
  • DIRECTION
  • ROTATION
  • ELECTRO

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